Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives

Autores
Fernandez, Luciana Andrea; Santo, Marisa Rosana; Reta, Mario Roberto; Giacomelli, Liliana; Cattana, Rosa Irene; Silber, Juana; Risso, Mariela; Cerecetto, Hugo; Gonzalez, Mercedes; Olea-Azar, Claudio
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The relationship between the herbicidal activity of a number of novel 1,2,5-oxadiazole N-oxides and some physicochemical properties potentially related with this bioactivity, such as polarity, molecular volume, proton acceptor ability, lipophilicity, and reduction potential were studied. The semiempirical molecular orbital method AM1 was used to calculate theoretical descriptors such as dipolar moment, molecular volume, Mulliken´s charge and the octanol/water partition coefficients (log Po/w). The values of the reduction potentials (Er) were obtained by cyclic voltammetry. In addition, the retention factors (log k’w) on a reversed-phase high-performance liquid chromatography (RP-HPLC) column in pure aqueous mobile phases were measured for several N-oxide derivatives. The log k’w values show good correlation with the calculated values of log Po/w, showing that the chromatographic parameter can be used as lipophilicity descriptor for these compounds. The multiple regression analysis between the descriptors for the N-oxide derivatives and the herbicide activity indicate that the variance in the biological activity can be explained by changes in the lipophilicity and in the reduction potential.
Fil: Fernandez, Luciana Andrea. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina
Fil: Santo, Marisa Rosana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Reta, Mario Roberto. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Giacomelli, Liliana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Cattana, Rosa Irene. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Silber, Juana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Risso, Mariela. Universidad de la República; Uruguay
Fil: Cerecetto, Hugo. Universidad de la República; Uruguay
Fil: Gonzalez, Mercedes. Universidad de la República; Uruguay
Fil: Olea-Azar, Claudio. Universidad de Chile; Chile
Materia
HERBICIDES ACTIVITY
N-OXIDES
LIPOPHILICITY
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/115641
Acceder
id CONICETDig_5eeeb30c339f8b02dde09559313cf1b4
oai_identifier_str oai:ri.conicet.gov.ar:11336/115641
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide DerivativesFernandez, Luciana AndreaSanto, Marisa RosanaReta, Mario RobertoGiacomelli, LilianaCattana, Rosa IreneSilber, JuanaRisso, MarielaCerecetto, HugoGonzalez, MercedesOlea-Azar, ClaudioHERBICIDES ACTIVITYN-OXIDESLIPOPHILICITYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The relationship between the herbicidal activity of a number of novel 1,2,5-oxadiazole N-oxides and some physicochemical properties potentially related with this bioactivity, such as polarity, molecular volume, proton acceptor ability, lipophilicity, and reduction potential were studied. The semiempirical molecular orbital method AM1 was used to calculate theoretical descriptors such as dipolar moment, molecular volume, Mulliken´s charge and the octanol/water partition coefficients (log Po/w). The values of the reduction potentials (Er) were obtained by cyclic voltammetry. In addition, the retention factors (log k’w) on a reversed-phase high-performance liquid chromatography (RP-HPLC) column in pure aqueous mobile phases were measured for several N-oxide derivatives. The log k’w values show good correlation with the calculated values of log Po/w, showing that the chromatographic parameter can be used as lipophilicity descriptor for these compounds. The multiple regression analysis between the descriptors for the N-oxide derivatives and the herbicide activity indicate that the variance in the biological activity can be explained by changes in the lipophilicity and in the reduction potential.Fil: Fernandez, Luciana Andrea. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; ArgentinaFil: Santo, Marisa Rosana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Reta, Mario Roberto. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Giacomelli, Liliana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Cattana, Rosa Irene. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Silber, Juana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Risso, Mariela. Universidad de la República; UruguayFil: Cerecetto, Hugo. Universidad de la República; UruguayFil: Gonzalez, Mercedes. Universidad de la República; UruguayFil: Olea-Azar, Claudio. Universidad de Chile; ChileMolecular Diversity Preservation International2005-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/115641Fernandez, Luciana Andrea; Santo, Marisa Rosana; Reta, Mario Roberto; Giacomelli, Liliana; Cattana, Rosa Irene; et al.; Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives; Molecular Diversity Preservation International; Molecules; 10; 9; 9-2005; 1197-12081420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390%2F10091197info:eu-repo/semantics/altIdentifier/url/https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147555/info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:19:04Zoai:ri.conicet.gov.ar:11336/115641instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-10 13:19:04.974CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives
title Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives
spellingShingle Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives
Fernandez, Luciana Andrea
HERBICIDES ACTIVITY
N-OXIDES
LIPOPHILICITY
title_short Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives
title_full Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives
title_fullStr Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives
title_full_unstemmed Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives
title_sort Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives
dc.creator.none.fl_str_mv Fernandez, Luciana Andrea
Santo, Marisa Rosana
Reta, Mario Roberto
Giacomelli, Liliana
Cattana, Rosa Irene
Silber, Juana
Risso, Mariela
Cerecetto, Hugo
Gonzalez, Mercedes
Olea-Azar, Claudio
author Fernandez, Luciana Andrea
author_facet Fernandez, Luciana Andrea
Santo, Marisa Rosana
Reta, Mario Roberto
Giacomelli, Liliana
Cattana, Rosa Irene
Silber, Juana
Risso, Mariela
Cerecetto, Hugo
Gonzalez, Mercedes
Olea-Azar, Claudio
author_role author
author2 Santo, Marisa Rosana
Reta, Mario Roberto
Giacomelli, Liliana
Cattana, Rosa Irene
Silber, Juana
Risso, Mariela
Cerecetto, Hugo
Gonzalez, Mercedes
Olea-Azar, Claudio
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv HERBICIDES ACTIVITY
N-OXIDES
LIPOPHILICITY
topic HERBICIDES ACTIVITY
N-OXIDES
LIPOPHILICITY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The relationship between the herbicidal activity of a number of novel 1,2,5-oxadiazole N-oxides and some physicochemical properties potentially related with this bioactivity, such as polarity, molecular volume, proton acceptor ability, lipophilicity, and reduction potential were studied. The semiempirical molecular orbital method AM1 was used to calculate theoretical descriptors such as dipolar moment, molecular volume, Mulliken´s charge and the octanol/water partition coefficients (log Po/w). The values of the reduction potentials (Er) were obtained by cyclic voltammetry. In addition, the retention factors (log k’w) on a reversed-phase high-performance liquid chromatography (RP-HPLC) column in pure aqueous mobile phases were measured for several N-oxide derivatives. The log k’w values show good correlation with the calculated values of log Po/w, showing that the chromatographic parameter can be used as lipophilicity descriptor for these compounds. The multiple regression analysis between the descriptors for the N-oxide derivatives and the herbicide activity indicate that the variance in the biological activity can be explained by changes in the lipophilicity and in the reduction potential.
Fil: Fernandez, Luciana Andrea. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina
Fil: Santo, Marisa Rosana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Reta, Mario Roberto. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Giacomelli, Liliana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Cattana, Rosa Irene. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Silber, Juana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Risso, Mariela. Universidad de la República; Uruguay
Fil: Cerecetto, Hugo. Universidad de la República; Uruguay
Fil: Gonzalez, Mercedes. Universidad de la República; Uruguay
Fil: Olea-Azar, Claudio. Universidad de Chile; Chile
description The relationship between the herbicidal activity of a number of novel 1,2,5-oxadiazole N-oxides and some physicochemical properties potentially related with this bioactivity, such as polarity, molecular volume, proton acceptor ability, lipophilicity, and reduction potential were studied. The semiempirical molecular orbital method AM1 was used to calculate theoretical descriptors such as dipolar moment, molecular volume, Mulliken´s charge and the octanol/water partition coefficients (log Po/w). The values of the reduction potentials (Er) were obtained by cyclic voltammetry. In addition, the retention factors (log k’w) on a reversed-phase high-performance liquid chromatography (RP-HPLC) column in pure aqueous mobile phases were measured for several N-oxide derivatives. The log k’w values show good correlation with the calculated values of log Po/w, showing that the chromatographic parameter can be used as lipophilicity descriptor for these compounds. The multiple regression analysis between the descriptors for the N-oxide derivatives and the herbicide activity indicate that the variance in the biological activity can be explained by changes in the lipophilicity and in the reduction potential.
publishDate 2005
dc.date.none.fl_str_mv 2005-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/115641
Fernandez, Luciana Andrea; Santo, Marisa Rosana; Reta, Mario Roberto; Giacomelli, Liliana; Cattana, Rosa Irene; et al.; Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives; Molecular Diversity Preservation International; Molecules; 10; 9; 9-2005; 1197-1208
1420-3049
CONICET Digital
CONICET
url http://hdl.handle.net/11336/115641
identifier_str_mv Fernandez, Luciana Andrea; Santo, Marisa Rosana; Reta, Mario Roberto; Giacomelli, Liliana; Cattana, Rosa Irene; et al.; Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives; Molecular Diversity Preservation International; Molecules; 10; 9; 9-2005; 1197-1208
1420-3049
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390%2F10091197
info:eu-repo/semantics/altIdentifier/url/https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147555/
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1842981037969244160
score 12.48226

Publicaciones similares